


tentacle boyfriends do it better

by septiplier500



Category: Video Blogging RPF, Youtube RPF
Genre: Anal Gaping, Anal Sex, Autoerotic Asphyxiation, Bondage, Choking, Crossdressing, M/M, Tentacle Monsters, Tentacle Sex, Tentacles, Urethral Play
Language: English
Status: Completed
Published: 2016-11-22
Updated: 2016-11-22
Packaged: 2018-09-01 13:48:16
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,707
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8626918
Author URL: https://archiveofourown.org/users/septiplier500/pseuds/septiplier500
Summary: Jack is lonely, sexually frustrated, and completely overlooking the boyfriend he already seems to have. Sam makes a point to educate him on his mistake.





	

Jack groans in frustration and yanks his earbuds out, tossing his phone – headphones still attached – at the pile of blankets he’d kicked down to the end of his mattress. He yanks his pillow out from under his head and crams it over his face to groan out his annoyance, heedless of his lube-sticky fingers smearing the age-faded cotton of the pillow case.

It was _bullshit_. He just wanted to watch some porn, jack off and finger himself a little, and reap the benefits of his usual post-orgasm burst of energy. He had some traveling coming up and needed to triple his output to compensate for not recording for a few days, but he was so tired. _He needed to come_. It was the only thing that settled his nerves.

After another long, angry groan, Jack tosses the pillow aside and rolls onto his belly. If the internet won’t supply him with any decent porn, he’ll just… _improvise_. He already sort of was, having dug a pair of sheer stockings – reserved for his subbiest of moods – out of his closet before even starting. He’d bought them online on a whim, and they were perfect for the occasional danger wank, even though there was zero risk of anyone ever actually catching him at it.

He likes the way they feel, silky and tight, tugging at his leg hair if he doesn’t move the right way. He’d shaved his legs, originally, but he sort of likes it better leaving his hair alone. It’s the same as when he wears bras, lifting his arms and staring at the contrast of the fluff at his armpits versus the lace clutching his pecs. The duality, or whatever.

Jack gets up on his knees but keeps his face on the bed, tucking his head so he can keep his forehead to the mattress for balance. With his hands free, he slides on arm around his hip to get to his ass, and reaches down with the other to hold his dick. He’s barely half-hard, dick as disappointed with all the crappy bondage porn as _he_ was, so he takes his time stroking himself, letting his foreskin do most of the work.

His asshole’s already a little loose, puckered skin parting easily when Jack pushes half a finger back in. He should really spring for a dildo, but he’s always craved warmth in his ass; maybe a glass one that he can heat up or something. For now he relies on his own fingers even though the angle sucks, fitting two more beside the first without even trying – it’s getting them deep enough to really _ream_ himself that’s the complicated bit.

And that’s kind’ve the whole problem.

He plays like that for a little while, trying to imagine what it would like to have someone there, stuffing him full and really railing him. He imagines different ex-girlfriends pinning him down and opening him up on their pretty little fingers, making him arch his ass to be spitted on a thickly endowed strap-on. He imagines being in college again and some of his guy crushes coming across him jerking off, pictures them taking turns fucking him hard and fast, filling him with come but not even bothering to touch his prostate in the process. Imagines his abused asshole gaping afterward, the emptiness driving him mad with need, and begging his fantasy lovers to let him get off. Imagines being forced to take an entire fist to earn it.

He’s hard now, of course he fucking is, cramming his fingers as deep as he can and opening them up to stretch his asshole as much as possible at this angle… But he’s not getting anywhere. He’s leaking in his hand, thighs shaking with how wide he’s got his knees placed, but he’s nowhere near coming. It’s _not enough_.

Maybe it’s the anxiety of impending travel. Maybe it’s that he’s sick of doing this all by himself.

And fuck, Jack’s been so lonely the past few months. It’s the whole reason why he said yes to another trip, even though he hates the whole process of traveling, and usually hates the cities he ends up in. He wants to get out of his house and see his friends and make new ones, soak up all the warm hugs and awkward horsing around that comes with it all.

And – he’s not going to _cry_ right now, with his fingers up his ass and his dick hard enough to nail his own coffin shut, wearing fucking stockings, _Jesus_. Here lies Jack, a little lonely crybaby who spent way too much time imagining having real life conversations, and also being a cumdumpster.

Groaning at himself, Jack pulls his fingers free and carelessly wipes them off on his sheets. He’s past due on doing some laundry anyhow. “Jesus,” he slurs, rubbing at his eyes with the butt of his palm, “How fuckin’ sad am I?”

He actually gets an answer, in the form of a consoling purr from Sam. Or, as much as Sam can purr – he hasn’t got any vocal chords, so it’s more of a deep, hum-like rumbling. Jack looks down to see Sam slinking out from under his bed like a the clever little land octopus he is, his large, gleaming eye slowly blinking up at Jack. Chastising.

“Don’t look at me like that, ya little scamp,” Jack says, laughing as much at himself as he is at Sam, “Let me feel pathetic for a bit, I’ve fuckin’ _earned_ it.”

Jack scoots over to sit on the edge of his bed, dropping down a stockinged foot to pet his toes over the largest of the tentacles that Sam’s sporting today. Sam’s a funny little creature, swelling and shrinking his body size on a whim, producing and retracting tentacles depending on what needs climbing. Jack finds him all over the house, tucked up on high shelves or nestled in empty pots in the cabinet or sprawled out on the furniture, napping like a cat in the sun. Jack’s used to him wandering as he pleases and isn’t surprised he was under the bed.

Sam continues purring, a smaller tentacle gliding up around Jack’s ankle to return the affection. Sometimes his skin – hotter than a human’s and much more rubbery – is damp with a mucusy kind’ve film, but today it’s sleek and dry, and Jack sort of likes the way it feels shifting over his stocking-covered leg.

And, sure, he’s thought about Sam like that before. He’s had internet access for _ages_ , and tentacle porn’s existed since the BC’s. But he’s always pushed it out of his head, too used to thinking of Sam as his sassy eyeball cat thing to ever let a passing pervert moment change how he sees the little guy. It’s _Sam_. His best little buddy.

Which is why it’s bruising not just to his skull, but to his _ego_ , when Sam’s tentacle firms up on his ankle and yanks. His head hits the wall as he slides forward, his ass hanging off the mattress but the small of his back still on the bed. “Sam, what the _fuck_!” Jack yells, trying to kick Sam’s grip off – but Sam just wraps another tentacle around his other ankle and yanks his legs apart, holding them up off the ground so that his ass is lifted higher that the bed.

Jack can’t kick, the muscles in Sam’s tentacles are like liquid steel. He tries sitting up instead, first getting up on his elbows, but another tentacle slithers up over the other side of the bed and grabs his bicep, yanking him off balance. He falls back on the bed and finds both of his arms being taken, thick green limbs slithering out of nowhere and winding around his wrists. His hands are dragged back towards the space between his mattress and the wall, knuckles bumping the wall before Sam stops pulling.

“Sam,” Jack says, chest heaving as he struggles against the urge to panic, “Yer _seriously_ scarin’ th’ _shit_ outta me, man.”

Sam uses some of his tentacles – and there’s way more than five, what the fuck – to hoist himself up on the bed, crowding Jack’s hip. He starts purring again, blinking at Jack with almost childlike false innocence, like, who, me? It’s the same look he makes when he’s broken something or almost made Jack trip by slinking between his feet when he’s walking, and it’d be cute if he wasn’t holding Jack hostage in his own damn bedroom.

“I really don’t know what th’ fuck yer tryin’ t’ do,” Jack says. He’s got some ideas, but he’s desperately willing his stupid brain away from weirdo territory before he starts really freaking out. This is _Sam_ he’s dealing with.

Sam’s purring gets louder, and he butts into Jack’s hip. He starts patting Jack’s belly with a few smaller tentacles, blatantly imitating the way Jack pets him. It’s fucking weird. And Jack’s still kind’ve hard, cock flopped on his thigh, a little bit sticky with lube and precum that’s gone all tacky with age.

“Sam, buddy, this isn’t normal,” Jack tries, but he ends up laughing a little before he can finish his sentence, because Sam himself isn’t exactly normal either. As much as Jack tries treats him like a quirky, aloof cat with no fur and a lot of mischief, he’s not a cat.

And that’s when Sam starts playing with his dick.

It seems accidental, initially, like Sam just doesn’t realize where his petting has drifted. But even when Jack grunts in surprise, Sam doesn’t stop, tentacle thinning out and winding its way around the base of Jack’s shaft. Sam’s limb muscles clench and release, the pressure making Jack’s toes curl immediately. “Fuck,” Jack gasps. The tentacle glides higher, pointed tip dipping into Jack’s foreskin like the teasing flick of a tongue. “Sam, buddy, seriously,” Jack groans, eyes squeezing shut, “I think yer a little confused right now!”

Sam’s purring gets noisier, rumbling like a car engine.

And Jack’s confused but he’s not stupid, he knows what comes next, even if it’s hard to conceptualize coming from his fucking p-– no, he can’t even think of Sam as a pet right now, it’s too _weird_.

The tentacle that snakes beneath his thigh is different than the rest – it’s got that filmy dampness Jack sometimes notices, and he can only see it a little by craning his head, but its green is deeper, darker than the other limbs. There’s more veins, maybe, the denser bloodflow making its color richer and its skin much hotter. It pushes wetly through the lube leaking out of Jack’s ass and Jack compulsively cringes at the noise, asshole clenching tight.

Sam pats his belly again, crooning sweetly. When Jack risks glancing down again, he finds Sam watching him curiously, unoccupied tentacles roiling idly behind his wide eye. Jack swallows but doesn’t look away again, and just when he starts feeling the strain in his neck, a tentacle coils up behind his head to keep it cushioned.

“Considerate of ya,” Jack says sarcasticly, and Sam doesn’t even have the decency to pretend to be bashful like he does when he’s in trouble for stealing Jack’s snacks. “Jesus, an’ I thought _I_ was th’ one that outta feel ashamed today,” Jack grumbles, fighting back a grin, “Lookit you, not even buyin’ me dinner first.”

Sam hums, putting pressure on Jack’s asshole. It’s already sore from how carelessly Jack had been fucking himself earlier, and Jack’s face goes hot when his cock twitches in Sam’s grasp. He likes that it hurts, likes that he’ll probably be so sore afterward he’ll have to put a pillow on his desk chair, likes that he’ll have to go to sleep on his belly with his ass up in the air, maybe with Sam still watching him from the shadows…

“Fuck,” Jack groans, rolling his hips, “Fuck, _okay_ , put it in me already.”

The tentacle pushes in smoothly, greased by its own moisture as well as lingering lube. As it glides inside it undulates, pressing against Jack’s tender inner walls like it’s testing how much it can stretch Jack from the inside. Jack’s head falls back, held aloft only by Sam’s tentacle, and he keens low in his throat. Sam takes the noise as the encouragement it was intended to be, and begins coiling the limb inside him, folding over itself to stuff Jack fuller than he’s ever been before. The very tip loops back and settles against his prostate, firmly nuzzling the delicate flesh, a gesture that has Jack spurting precum all over the tentacle holding his dick.

“Oh fuck,” Jack whines, trying to arch harder against the wriggling tentacle working inside him, desperate for more even as he struggles to accommodate what he’s already been given. “Sam,” he groans, face flushing when he realizes how easily the name rolls off his tongue like this. It’s nothing like calling for him in a sing-song when he’s got dinner ready for him, or when he’s trying to find where Sam’s been hiding out all day. “Fuck,” he breathes, ass clutching at the hot, shifting girth inside him, “Oh, shit, _Sam_.”

Abruptly, his wrists are released, even though he hadn’t even tried fighting against Sam’s hold. Jack shakes his head to try and think through the sex haze and eases up on his elbows, peering down at the still continuously purring little bastard cuddled into his hip. Sam’s still watching him, avidly.

“Okay!” Jack says loudly, face flushing darker, “I get it, I wasn’t respectin’ yer sentience, treatin’ ya like a goddamn _pet_. I’m a bad friend, I’m sorry.” He’s panting before he’s finished, embarrassment and shame stinging at the back of his throat because it’s all true. He was so busy whining about wishing he had real human company, he overlooked the company he already had.

Sam blinks slowly as though in pleasure, and his purrs take on a higher pitch. It’s a fair bit like mogwai singing, if Jack’s being honest. The sound bottoms back out again into its usual low rumble, and Jack yells as a tentacle wraps around his ribcage and rolls him over onto his side.

Sam’s grip on his legs is loose so Jack flails briefly, no longer fully supported, and drops one foot to the floor for balance. His stocking makes it difficult to find purchase on the floor, toes slipping, but he manages to steady himself without pulling anything. Sam wraps his tentacle tightly around the other leg to hoist it up, the position spreading the cheeks of Jack’s ass better for Sam’s view.

Because Sam is definitely watching his own tentacle bugger the fuck out of Jack’s asshole. Oh _Jesus_.

“Fuck me,” he pleads, the words pouring out in a desperate rush, “Sam, please, fuck me.” Sam lifts a tentacle to stroke Jack’s ruddy cheek, and Jack turns his face into the touch, rubbing against him gratefully.

The tentacle on his dick starts working the shaft in earnest, tip slithering over Jack’s piss slit, testing his reaction. Jack moans, loud and throaty, before he can really consider the question – and the tip nudges in, damp and burning. Jack pushes himself up onto his hands, moving his hips to accept penetration from both sides, his eyes half-lidded as he watches Sam.

“Does this feel good for you too?” Jack asks, soft and breathless. He can feel Sam’s heat so deep in himself it feels like maybe his insides have been rearranged to suit Sam’s needs, and it’s breath-takingly intimate, having something – someone, he corrects himself, inside him.

Sam doesn’t even blink.

Jack winces, apologetic, “That’s prolly a no – is there somethin’ else I can do, that feels good fer you?”

The appendage in his dick eases deeper, and Jack hisses and shudders, thrusting into the warm coils enveloping his cock. The one in his ass folds over itself again, somehow, and Jack feels like he might burst with it, his prostate practically bruised with how endless Sam’s milking presses are. Jack’s mouth falls open, and he’s vaguely aware he’s probably drooling a little, but he’s beyond feeling shy now, fucked too close to the end of oblivion. “Okay, I get it, it’s all about me,” he groans, fingers curling in his already stained sheets.

He turns his head, tongue lapping at the thin limb Sam’s been petting his cheek with. The wetness clinging to Sam’s skin is sharp and salty, a lot like Jack’s come but with a sweet undertone that makes him think of under-ripened fruit. He gets his mouth around it and sucks, swallowing, and Sam yanks his limb free.

“Hey!” Jack shrills, and Sam boops him on the nose. “I _said_ I got it, y'don’t got any sex organs – that was fer _my_ benefit, not yours!” he says crossly, craning his neck to chase the elusive little limb – and Sam lets him have it back, full-body shivering with silent laughter. Jack loves Sam’s laugh, even though it’s only ever directed at him, and he finds himself soaking it in as much as he’s soaking in the sex. He wants to make Sam laugh more.

But first he wants to get as much of Sam’s tentacle in his mouth as he can, turning his head and ducking down until the tip glosses the back of his throat and he coughs. Sam doesn’t relent, the cheeky bastard, and just inches deeper on his own as Jack swallows against the urge to gag. Briefly, Sam cuts off his ability to breathe, and Jack’s eyelashes flutter as his vision gets peppery around the edges. His whole body sings with it, blood pounding in his ears; there’s a similar but far faster rhythmic thud beating inside him wherever he can feel Sam’s limbs.

The tentacle holding his ribs shifts, the end slithering over a nipple and Jack starts, outrightly choking on his throatful. The probing digit thins out to better wrap around the tight little peak of Jack’s nipple, squeezing so tightly that Jack kicks his feet. Another tentacle coils up to perform the same trick on his other nipple, and Jack arches his back, offering his chest up for the abuse. He cries out continuously even as Sam’s got his screaming muffled, moving to fuck Jack’s throat quick and mean.

He’s going to come, he can feel it in the steady throb of his untouched balls. His ass is being fucked so wide he’ll probably be walking weird for a month, and his cock can’t even leak the precum he knows he’d be dribbling otherwise, the shaft stuffed full of tentacle instead. His nipples are being yanked and twisted relentlessly, Sam playing him like a goddamn musical instrument, like all his hollering is just his newest hit single or something, fuckin’ _Jesus_ –

Sam unplugs his cock and it immediately burns worse, piss slit gaping and finally able to drip. He doubles down on his efforts to stroke Jack off, and Jack starts bucking, writhing against all the pawing and pulling and fucking being done to his strung-up body, nails no doubt biting through the sheets he’s been clutching so desperately.

Another tentacle from the endless collection Sam’s apparently toting around somewhere wraps itself around his waist, thick band settling over his stomach. It clenches suddenly, gripping Jack’s struggling body and making him stay still and feel how fucking full he is. It’s the squeezing that finally does him in, screaming around his mouthful and shaking to goddamn pieces, his arms giving out and Sam reaching up with a few more limbs to hold him up.

He spurts all over his own chest and belly because that’s how Sam has his dick angled, a few thick drops pattering the tentacle wrapped around his middle. It’s like dying, his vision finally blacking out entirely and the fiery pain in his lungs flaring into numbness, stockinged legs kicking uselessly before draping limply in Sam’s grasp, all fight gone. Sam cradles him, taking his weight; his brutalized cock and nipples are released and the tentacle in his mouth retracting completely, thick trails of spit briefly following across Jack’s chin before snapping.

Sam settles him back on the bed, plucking his pillow up from wherever Jack had chucked it earlier and tucking it beneath his head. Jack can only watch, completely fucking dazed, struggling to relearn how to breathe in a world so different from the one he’d been in just an hour before.

Sam stops purring and starts singing again, easing out of the coils he’d wrapped up in inside Jack’s ass. Everything hurts like a hammer to the nervous system, but there’s relief too as Sam starts sliding out of his ass, Jack’s inner muscles relearning how to hold himself together without Sam’s stretch.

He’s leaking lube and the filmy, greasy stuff that’s got some of Sam’s limbs all wet, and there’s spit all over his face and chest, and he doesn’t give even half of a shit about what a mess he is. Honestly, he’s probably a sexy-looking mess anyway, totally fucking wrecked by his one person gangbang-y friend over there.

Sam’s singing hiccups out, replaced by another one of his silent shiver-laughs.

“Shut up,” Jack says indignantly, and his voice is so hoarse he barely sounds human, “I can be a sexy anime boy if I want to. I’ve got the hair _and_ the tentacle boyfriend now.”

Sam slinks up onto Jack’s stomach, body shrinking in size to accommodate the change of surface. He settles on Jack’s chest, unbothered by the continued heaving as Jack catches his breath.

“S'right,” says Jack, reaching up to pet the much smaller gaggle of tentacles happily pawing through his chest hair, ignoring the trembling in his fingers, “I said _boyfriend_. No taksies-backsies.” A yawns cracks his jaw and he exhales it slowly, enjoying the way it makes his throat ache like the worst of colds, only great. “Ya can’t do _that_ t’ a guy an’ not expect him t’ get attached.”

Sam laughs, tentacles twining lazily with Jack’s fingers.

Somewhere at the end of the bed, Jack can hear tinny moans vibrating on his headphones, his disappointing porn from earlier still playing. He closes his eyes and ignores it. 

**Author's Note:**

> Rebloggable version on Tumblr: http://septiplier500.tumblr.com/post/153403307522/tentacle-boyfriends-do-it-better (Maybe give my blog a look and consider following, eh?)
> 
> I'm seriously considering writing a sequel. In fact, I have a whole bunch of ideas for the adventures of Jack and his tentacle monster boyfriend. Would anyone be interested in reading that?


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